4-Methylmorpholine → tert-butyl (4S,7S,10aS)-7-(hydrazinecarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

HRID 529481Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:15][CH2:14][S:13][C@H:12]2[CH2:16][CH2:17][CH2:18][C@@H:19]([C:20](O)=[O:21])[N:11]2[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.[NH2:39][NH2:40]>C(Cl)Cl.CCOC(C)=O>[NH:39]([C:20]([C@H:19]1[N:11]2[C@@H:12]([S:13][CH2:14][CH2:15][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]2=[O:23])[CH2:16][CH2:17][CH2:18]1)=[O:21])[NH2:40]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid (121 mg, 0.351 mmol) and N-methylmorpholine (0.048 mL, 0.44 mmol) in DCM (2 mL) at 0° C. was added isobutyl carbonochloridate (0.053 mL, 0.40 mmol). The mixture was stirred at 0° C. for 40 min. Then, hydrazine (0.044 mL, 1.4 mmol) was added and the reaction was stirred at rt for 1 hr. The mixture was diluted with EtOAc and washed with water and saturated aqueous NaCl. The organic layer was separated, dried over MgSO4, filtered and concentrated to give tert-butyl (4S,7S,10aS)-7-(hydrazinecarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (125 mg, 0.349 mmol, 99% yield) as a white solid. Anal. Calcd. for C15H26N4O4S m/z 358.4. found: 359.1 (M+H)+.

Workup

stirringthe reaction was stirred at rt for 1 hr
washwashed with water and saturated aqueous NaCl
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6ff37e2b53294ce59270735399d44039
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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